Morpholine → HCID 59759195, compound

HRID 914313Notes

Reaction equation

HRID 914313 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]3[N:18]=[C:19]([S:22][C:23]([CH3:32])([CH3:31])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[S:20][CH:21]=3)=[C:10]([C:33]([OH:35])=O)[CH:9]=2)=[CH:4][CH:3]=1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>ClCCl>[C:27]([O:26][C:24](=[O:25])[C:23]([S:22][C:19]1[S:20][CH:21]=[C:17]([CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9][C:10]=2[C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[O:35])[N:18]=1)([CH3:31])[CH3:32])([CH3:28])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59759162HCID 59759162, compound

Product 1

HCID 59759195HCID 59759195, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4′-Fluoro-4-(2-{2-[(2-tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethoxy)biphenyl-3-carboxylic acid (170 mg) obtained in Example 93-1 and morpholine (43 mg) were dissolved in dichloromethane (2 mL), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDC) hydrochloride (94 mg) and 1-hydroxybenztriazole (HOBt) monohydrate (75 mg) were successively added, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1) to give the title compound (180 mg) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-fd605e0118d741e9a82b28403eddd560
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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